Bleaching of carboxylic acid esters and/or epoxy compounds employing ultraviolet light

ABSTRACT

A process of bleaching carboxylic acid esters and/or epoxy compounds by irradiating the esters and/or epoxy compounds with ultraviolet light in the presence of a peroxy compound. The preferred compounds bleached are the epoxidized higher fatty acid esters. Hydrogen peroxide and peracetic acid are examples of suitable peroxy compounds.

United States Patent French et a]. [4 1 June 6, 1972 BLEACHING OF CARBOXYLIC ACID [56] References Cited ESTERS AND/OR EPOXY COLIPOUNIB EMPLOYING ULTRAVIOLET LIGHT UN'TED STATES PATENTS l 948 28] 2/1934 Smith ..204/l58 [72] lnventors: William H. French, St. Paul; Oliver A. Os-

sanna, Bloomingmn, both of Minn. 2,647,868 8/1953 Dean ..204/ l 58 Assignee: Ashlllld Primary Examiner-Howard S. Williams [22] Filed: Feb 2, 1971 Attorney-Walter H. Schneider 2| App]. No.: 112,088 57 ABSTRACT A process of bleaching carboxylic acid esters and/or epoxy [52] US l- W158 R compounds by irradiating the esters and/or epoxy compounds [51] Int. Cl. ..B0lj 1/10 with ultraviolet light in the presence of a peroxy compound. [58] Field of Search ..204/ 158 The preferred ompounds bleached are the epoxidized higher fatty acid esters. Hydrogen peroxide and peracetic acid are ex- I amples of suitable peroxy compounds.

16 ClaimsQNo Ih'awings BLEACHING OF CARBOXYLIC ACID ESTERS AND/OR EPOXY COMPOUNDS EMPLOYING ULTRAVIOLET LIGHT BACKGROUND OF THE INVENTION This invention relates to a process for bleaching organic carboxylic acid esters and/or epoxy compounds.

Various carboxylic acid esters and epoxidized compounds have been widely used as plasticizers, stabilizers, and surface active agents. Of particular significance are the epoxidized fatty acid esters which enjoy commercial acceptance as suitable plasticizers for various synthetic polymers, and particularly for vinyl chloride containing polymers, such as polyvinyl chloride.

Generally, the carboxylic acid esters and epoxy compounds are discolored as initially obtained from the usual commercial methods of preparation. It is quite important, however, that these materials have as light a color as possible. This is particularly crucial when they are to be used as plasticizers, stabilizers, and surface active agents. Therefore, various processes have been developed in an attempt to produce materials having reduced color levels.

Included among such prior decolorization processes are treatment with caustic; and adsorption of color by either activated carbon, alumina, silica gel, or treated clays. Most of these prior decolorization techniques, however, do not effectively reduce the color of the material to provide products of acceptable light color, such as a color of less than 100 APHA (American Public Health Association Scale). In addition, some treated clays are highly acidic, and therefore may cause decomposition of the epoxides resulting in loss of the product.

Of the above-mentioned methods, the most effective heretofore has been the caustic treatment. However, such a process suffers from the disadvantage in that it is necessary to wash the material with an aqueous solution after it has been refined with the caustic. In addition, this process presents a problem of separating two phases which are formed during the process. The separation in turn causes loss of some of the product.

In addition there have been some suggestions in the prior art to decolorize certain specific esters employing ultraviolet light alone. For example, see U.S. Pat. Nos. 1,948,281 and 2,647,868. However, such methods have not achieved any appreciable commercial acceptance. The use of ultraviolet light alone although somewhat effective for certain esters is not very effective in bleaching various commercially important esters and epoxides. In particular, ultraviolet light alone as will be shown hereinbelow is not very effective in bleaching certain epoxidized fatty acid esters. Also it is even known that ultraviolet light actually darkens some esters. For example, see U.S. Pat. No. 1,179,414.

The process of the present invention overcomes these disadvantages and provides a bleaching process for carboxylic acid esters and/or epoxy compounds which is relatively inexpensive, quite efficient, and easily performed in a short time.

BRIEF DESCRIPTION OF THE INVENTION The process of this invention comprises bleaching of an organic carboxylic acid ester and/or an epoxy compound by irradiating the carboxylic acid ester and/or epoxy compound with ultraviolet light in the presence of at least one peroxy compound.

DESCRIPTION OF THE PREFERRED EMBODIMENTS The process of this invention is suitable for bleaching or- Some suitable monohydricsaturated aliphatic alcohols providing the alcohol moiety of the ester include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, amyl, isoamyl, hexyl, heptyl, octyl, nonyl and decyl alcohols.

Some suitable dihydric alcohols include among others the lower glycols such as ethylene glycol, 1,2-propanediol, 1,3- propanediol, diethylmethylene glycol, trimethylene glycol, tetramethylene glycol, hexamethylene glycol, 1,3-butanediol, l,4-butanediol, and 2,3-butanediol.

Some suitable aliphatic alcohols which contain from 3 to 6 alcohol groups include glycerol, erythritol, pentaery-thritol, dipentaerythritol, and hexitols, such as mannitol and sorbitol.

In addition benzenoid alcohols having less than 10 carbon atoms may be employedas the alcohol moiety in the acid esters of the present invention. Such alcohols include benzyl, phenyl,.2-phenylethyl, l-phenylethyl, and nuclear methylated phenyl alcohols. Also cycloaliphatic alcohols such as cyclohexanol can be employed as the alcohol moiety in the esters used herein.

The process of this invention is'quite effective for bleaching fatty acid esters, polyesters, and most effective for bleaching epoxidized fatty acid esters.

Generally, the acid esters are esters of fatty acid having eight to 22 carbon atoms. Of particular importance are the triglycerides such as the animal, vegetable, and marine oils, and the corresponding epoxidized oils.

Some suitable fatty acids include caprylic, pelargonic, lauric, myristic, palmitic, stearic, behenic, oleic, linoleic, linolenic, ricinoleic, and erucic acids.

Examples of some suitable fatty acid esters are tallow, soybean oil, linseed oil, tall oil esters, safflower oil, perilla oil, sunflower oil, sperm oil, menhaden oil, and cottonseed oil.

Some examples of other suitable carboxylic acid esters are the various esters of phthalic acid and of adipic acid which are known plasticizers, such as dibutyl phthalate, dihexyl phthalate, dioctyl phthalate, didecyl phthalate, dibutyl adipate, dihexyl adipate, dioctyl adipate and didecyl adipate.

The polyesters which can be bleached by the present process include the well-known polycondensation products of polybasic acids and polyhydric alcohols. Numerous polyesters are commercially available and are adequately described in the literature including various U.S. Patents. For example, a-

carbon atoms and most often from about four to about 20 carbon atoms.

The preferred compounds are the epoxidized fatty acid esters of which epoxidized soybean oil and epoxidized tall oil esters are the most preferred. The epoxidized fatty oil esters generally have an oxirane content of about 3.5 to 9.5 percent and an iodine value less than 4.

' These epoxidized fatty acid esters which are bleached according to the present invention are commercially available and are readily obtainable by known methods fully described in numerous U.S. and foreign patents. For example, see U.S. Pat. Nos. 2,458,484 and 2,569502. Of particular interest are the epoxidized compounds obtained by the reaction of the corresponding ethylenically unsaturated acid or ester with a strong oxidizing agent such as peracetic acid or hydrogen peroxide in an acid medium for upwards to 15 hours. In such a process the acid or ester is substituted as the site of unsaturation with an oxirane oxygen.

These-epoxidized materials as obtained from such a process 7 are discolored and should be bleached if they are to be employed as plasticizers, stabilizers, and/or surface active agents. For example, an epoxidized ester such as epoxidized soybean oil may contain the following impurities which may contribute to the color of the epoxidized fatty acid ester:

1. phospholipides such as. lecithin, cephalin, and sphingomyelin;

. 2. sterols such as cholesterol, stigmasterol, and ergosterol;

3. tocopherols',

4. lipochrornes such as l-gossypol;

5. carotenoids (polyene pigments) such as lycopene, gamma carotene, beta carotene, alpha carotene, and zanthophylls; and

6. chlorophyll.

Although these above materials may be present in the epoxidized oil in merely trace amounts or even present in quantities that are not measurable, their discolorization effect can be quite noticeable. Accordingly, even a slight decrease in the quantity of the impurities over the prior art can have a tremendous effect upon the usefulness of the compound. Also, since the decoloring impurities may be present in such small quantities, their removal is quite difi'lcult. Some examples of suitable peroxy compounds useful in the present invention include hydrogen peroxide and peracetic acid.

The peroxy compound is most conveniently added as an aqueous solution. Some aqueous peroxide solutions contain from about 20 to about 90 percent by weight of the peroxy compound. Preferably the aqueous peroxide solution should contain between about 50 and about 70 percent by weight of hydrogen peroxide or should contain between about 20 an about 40 percent by weight of peracetic acid.

The minimum quantity of peroxy compound which can be present in the process is about 0.1 percent by weight based upon the ester and/or epoxy compound. Amounts less than thisquantity willnot be sufficient to provide a noticeable reduction'in the color of the ester and/or the'epoxy compound. The maximum quantity of peroxy compound that may be employed in the present process is about 3.5 percent by weight based upon the ester and/or epoxy compound. The peroxy compound can be employed in amounts greater than 3.5 percent by weight based upon the material being bleached. However, the possible advantages gained by using such quantities should be weighed against the disadvantages of higher amounts such as economics, reduced safeness, and subsequent problems of removal from the desired product. The preferred quantities of peroxy compound are between about 0.5 and about 2.0 percent by weight based upon the weight of the ester and/or epoxy compound.

' The total quantity of water which can be present during the processcan be as much as about percent by weight based upon the weight of the compound being bleached. lf quantities above 10 percent by weight based upon the material being bleached are present, then the treatment .will be ineffective since the dilution will be too great for an effective bleach. Also material will be lost due to emulsification of the ester or epoxy compound. It is desirable to employ at least some water in the process (e.g., 0.25 percent by weight of the material being bleached) for safety reasons, since in the absence of water an explosive mixture could possibly result from the peroxy compound and the ester or epoxy compound in combination. The preferred quantities of water to be present during the process are from 1 to about 5 percent by weight based upon the weight of the ester and/or epoxy compound.

it has further been found that when the material to be bleached is an epoxidized fatty acid ester, the present process can be unexpectedly improved by carrying out the irradiation in the conjoint presence of hydrogen peroxide and an alkaline material.

' bonate. For best results, .the alkaline material should be water soluble. The preferred alkaline materials are the sodium materials because of their color stability properties. For instance, if small amounts of such alkaline materials as potassium hydroxide, barium hydroxide, and ammonium hydroxide remain in the product after bleaching, they may tend to discolor the product a little if exposed to high temperatures for any great length of time. On the other hand, the sodium materials are not likely to cause any discoloration.

The minimum quantity of alkaline material when employed, to provide a noticeable reduction in the color of the material, is about 0.1 percent by weight based upon the epoxidized fatty acid ester. The maximum quantity of alkaline material that may be employed in the present process is about 2 percent by weight based upon the epoxidized fatty acid ester. Quantities greater than 2 percent by weight based upon the epoxidized material are not desirable since large losses of the desired product may occur. Such losses may be due to emulsification of some of the epoxidized fatty acid ester and also may be due to saponification of the epoxidized fatty acid ester. Of course, some loss of product can be tolerated with the maximum amount being determined by practical and economical considerations. The preferred quantities of alkaline material when employed are between about 0.3 and about 0.8 percent by weight based upon the weight of the epoxidized fatty. acid ester. Preferably, the alkaline material is added as a dilute aqueous solution. Suitable concentrations of aqueous solution contain from about 2.5 to about 15 percent by weight of the alkaline material. I

' Also, in order for the presence of the alkaline material to provide a noticeable reduction in the color of the epoxidized fatty acid ester, it must be added in an amount to provide a pH of the reaction mass which is being bleached that is basic (pH greater than 7); Preferably the pl-l should be at least about 9.

In order to obtain the unexpected benefits from the use of the alkaline material, it is crucial that the epoxidized fatty acid ester be irradiated in the conjoint presence of the alkaline material and the peroxy compound. For instance, if the epoxidizedfatty acid ester were first irradiated in the presence of a peroxy compound such as .the hydrogen peroxide, then washed free of the peroxy compound, and then irradiated in the presence of the alkaline material such as sodium hydroxide, the bleached product obtained would be no different than one obtained from irradiating in the presence of the peroxy the process -of this invention include those lamps which operate on the principle of either a zinc, cadmium, thallium, gallium, indium, carbon, mercury, zirconium, hydrogen, deuterium, xenon, or helium arc. Another possible source of radiant energy is direct sunlight since the radiation of the sun contains ultraviolet light. Suitable lamps to be used in carrying out the present invention include those commercially available, high-pressure mercury arc lamps having a total power capacity ranging from about 50 watts to about 10,000 watts and generally from about watts to about 600 watts.

The preferred lamps though are the low pressure mercury lamps having a total power capacity ranging from about 0.5

watts to about 50 watts. These lamps emit monochromatic light generally in the wavelength of about 2,537 angstroms and wavelengths of 3000 angstroms and 3550 angstroms with the addition of suitable phosphors. It is most convenient to employ ordinary fluorescent lamps which emit light of a wavelength of about 3,500 angstroms.

' A quite suitable apparatus used to carry out the process of this invention is a Rayonet photochemical reactor. Also, it

may be desirable to form thin films of the material to be bleached and then expose the thin films to the action of the ultraviolet light.

The bleaching process of this invention can be carried out over a wide temperature range. For example, the reaction can be carried out at temperatures ranging from about 20 to about 122 C. Atmospheric pressure is most conveniently employed in carrying out the process of this invention. However, higher or lower pressures can be used when desired.

The bleaching process of this invention has generally been carried out in about one-half hour to about 4 hours. Generally the time of bleaching will vary from about 1 hour and about 2% hours.

Of course, the time will be somewhat dependent upon the materials being bleached, the particular peroxy compound, the amount of peroxy compound, and the desired degree of bleaching. Also the time may vary according to the particular configuration of the reactor being used. For instance, the bleaching time for a process wherein thin films of the material to be bleached are formed and then the films are exposed to the action of ultraviolet light may be shorter than when using a Rayonet photochemical reactor.

Also, when employing an alkaline material according to that aspect of the present invention, it is possible to obtain excellent bleaching in greatly reduced times. For instance, certain epoxidized fatty acid esters can be bleached to an acceptable level within about or minutes.

The addition of the peroxy compound and the alkaline material, if used, can be achieved by any of the conventional means of intimately contacting two or more different materials. For example, the process can be readily carried out by merely mixing the materials together. Of course, the time necessary to achieve a desired level of bleaching can be decreased if instead of mere mixing, the materials are rapidly agitated. However, when using high agitation and high shear,-

care must be taken so that the epoxidized fatty acid ester and water present do not form an emulsion. The formation of an emulsion would consequently cause great problems in the separation of the bleached material from the other ingredients. If an emulsion forms, it may be necessary to employ a centrifuge to break the emulsion.

It was particularly unexpected that the peroxy compound was effective in the present process to bleach the epoxidized fatty acid esters. Since the epoxidized fatty acid esters have probably already been exposed for several hours (up to about 15 hours) to the action of strong oxidizing agents, such as the hydrogen peroxide and peracetic acid, it would be expected that the epoxidized fatty acid ester has been bleached as far as possible by oxidation. However, according to the present invention, when the epoxidized fatty acid ester is treated with the peroxy compound and the ultraviolet light, an excellent bleaching process is provided.

Although it has been suggested to bleach certain polymers of either maleic acid, maleic anhydrides, or water-soluble salts of maleic acid by irradiating a solution of the polymer, hydrogen peroxide, and a solvent, it could not be expected that the vastly different materials of the present invention would be bleached by irradiating in the presence of hydrogen peroxide. The impurities present in the above-mentioned polymers and those which may be present in the materials of the present invention are vastly different and are not considered equivalent. It is well known that the success of a bleaching operation is quite dependent upon the particular material which is being bleached. It cannot be predicted that a bleaching process suitable for one type of material will be useful for a vastly different type of material.

In fact, it has been disclosed that ultraviolet light does not influence bleaching of cellulose with hydrogen peroxide or oxygen. It is quite apparent that the co-action between ultraviolet light and hydrogen peroxide in a bleaching process is not predictable from one group of materials to another.

In order that the invention may be better understood the following examples are given in which the amounts are by weight unless the contrary is stated.

EXAMPLE 1 parts of an epoxidized octyl tallate having an oxirane content of 4.7 percent, an acid value of 0.7, and an iodine value of 3.9, and a color of 3 Gardner, and containing 6.6 percent by weight of a 30 percent aqueous peracetic acid solution are placed in the center of a Rayonet photochemical reactor containing 16 fluorescent lamps emitting black light at a wavelength of 3,500 angstroms and having a total power of 24 watts. The composition is continuously agitated with a magnetic stirrer. Upon irradiation with the ultraviolet light at a temperature of about 38 C. for a period of l '15 hours, the sample is bleached to a color of l-Gardner.

EXAMPLE 2 100 parts of the same epoxidized octyl tallate as used in Example but without any peroxy compound are placed in the center of a Rayonet photochemical reactor containing 16 fluorescent lamps emitting black light at a wavelength of 3,500 angstroms and having a total power of 24 watts. The composition is continuously agitated with a magnetic stirrer. Upon irradiation with the ultraviolet light at a temperature of about 38 C for a period of 3% hours, the sample still has a color of 3-Gardner.

EXAMPLE 3 100 parts of the same epoxidized octyl tallate as used in Example 1 containing 6.6 percent by weight of a 30 percent aqueous peracetic acid solution are placed in the center of a Rayonet photochemical reactor which does not contain any lamps emitting ultraviolet light. The composition is continuously agitated with a magnetic stirrer. Upon such treatment without the ultraviolet light at a temperature of about 38 C for a period of 2 hours, the sample still has a color of 3- Gardner.

EXAMPLE 4 100 parts of an epoxidized octyl tallate, having an oxirane content of 4.3, an acid value of 0.3, and an iodine value of 3.1, and a color of 2 Gardner, and containing 4 percent by weight of a 10 percent aqueous sodium hydroxide solution and 1.25 percent by weight of a 50 percent aqueous hydrogen peroxide solution are placed in the center of a Rayonet photochemical reactor containing 16 fluorescent lamps emitting black light at a wavelength of 3,500 angstroms and having a total power of 24 watts. The composition is continuously agitated with a magnetic stirrer. Upon irradiation with the ultraviolet light at a temperature of about 38 C for a period of one-fourth hour,

' the sample is bleached to a color of l-Gardner.

EXAMPLE 5 100 parts of an epoxidized soybean oil having an acid value of 0. 10, a hydroxyl value of 17, an iodine value of about 2.3, and a color of APHA, and containing 0.5 percent of a 30 percent aqueous peracetic acid solution are placed in the center of a Rayonet photochemical reactor containing 16 fluorescent lamps emitting black light at a wavelength of 3,500 angstroms and having a total power of 24 watts. The composition is continuously agitated with a magnetic stirrer. Upon irradiation with the ultraviolet light at a temperature of about 38 C for a period of 1 hour the sample is bleached to a color of 70 APHA and to a color of 60 APHA after 1% hours.

EXAMPLE 6 100 parts of the same epoxidized soybean oil as used in Example 5 but without any peroxy compound are placed in the center of a Rayonet photochemical reactor containing 16 fluorescent lamps emitting black light at a wavelength of 3,500 angstroms and having a total power of 24 watts. The composition is continuously agitated with a magnetic stirrer. Upon irradiation with the ultraviolet light at a temperature of EXAMPLE 7 100 parts of the same epoxidized soybean oil as used in Example and containing 0.5 percent of a 30 percent aqueous peracetic acid solution are placed in the center of a Rayonet photochemical reactor which does' not contain any lamps emitting ultraviolet light. The composition is continuously agitated with a magnetic stirrer. Upon treatment without the ultraviolet light at a temperature of about 49 C for a period of 1% hours, the sample is bleached to a color of 95 APHA.

A comparison of Example 1 with Examples 2 and 3 and a comparison of Example 5 with Examples 6 and 7 clearly show that the excellent results of the present invention are obtained with the combination of the ultraviolet light and the peroxy compound but are not attained with either alone. Also Example 4 shows the unexpected further improvement when employing both a peroxy compound and an alkaline material conjointly with the ultraviolet light.

The epoxidized materials bleached in the examples are obtained by epoxidizing the corresponding unsaturated material with hydrogen peroxide or peracetic acid for at least 10 hours in an acid medium according to known technology.

The results of the examples are set forth below in tabular form.

Original Final Ex. UV Addi- Time Color Color No. Light tive Hours APHA APHA l Yes Peracetic [.5 *3 *1- 2 Yes 7 None 3.5 Do "3 3 No Peracetic 2 Do *3 acid 4 I Yes H 0 V4 *2 l- NaOH 5 I Yes Peracetic l 105 70 acid Do Do I% Do 60 6 Yes None 1% Do I05 7 No Peracetic l 95 Do 95 acid Color is Gardner.

The APHA color is determined by a slightly modified ethod color comparison means with platinum-cobalt standards as originally established by the American Public Health Association and referred to by ASTM as Color of Clear Liquids" (Platinum-Cobalt Scale) in Designation D 1209-62. According to this method of color determination, a standard stocksolution of platinum and cobalt which will be referred to hereinbelow as No. 500 Stock Solution is prepared as follows:

a. 1.245 grams of potassium chloroplatinate (K PtCl analytical reagent, and 1.000 grams of Cobalt Chloride (CoCl, 6H O) American Chemical Society Grade (ACS Grade) are dissolved in distilled water in a 250 ml. volumetric flask;

b. 25 ml. of HCl (Sp. Gr. 1.18) ACS Grade are then added;

c. the solution is diluted to 250 ml. with distilled water;

d. the 250 ml. solution from step (c) is then transferred to a 1,000 ml. volumetric flask;

e. 75 ml. of HCl (Sp. Gr. 1.18) ACS Grade are then added;

and

f. the solution. is then diluted to 1,000 ml. with distilled water which has first been passed through the 250 ml. volumetric flask in order to wash out any residual chemicals therein. This l,000 ml. solution has a colorof 500 APHA. The 250 ml. solution from step (c) has a color of 2,000 APHA.

The color standards are then prepared from the No. 500 Stock Solution by diluting the requiredvolumes of No. 500 Stock Solution as set forth in the table below to 50 ml. with distilled water in 50 ml. tall form Nessler test tubes. Size No. l Kimble No. 453 15A or B.

No. 500 Stock Solution, Color Standard Number ml. APHA 0.5 5 1 l0 1.5 15 2 20 2.5 25 3 30 3.5 35 4 4O 5 50 6 60 7 70 I0 I00 15 150 20 200 25 250 30 300 35 350 40 400 45 450 50 500 ASTM color standards having the same colors as above are prepared by doubling the amount of the No. 500 Stock Solution as in table above, and diluted to 100 ml. in 100 ml. tall form Nessler test tubes, Size No. 2, Kimble No. 453 15A or B with distilled water.

The color of a sample is determined by filling a standard 50 ml. Nessler tube of thetype described above to the 50 ml. mark and then comparing it with the nearest working standard by looking vertically downward through the tube upon a white surface placed in such a position that non-glaring daylight is reflected through the column of liquid. Of course at night, regular daylight lamps can be used.

What is Claimed is: v

l. The process of bleaching a member selected from the group consisting of organic carboxylic acid esters, epoxy compounds and mixtures thereof, which comprises irradiating said compound with ultraviolet light. in the presence of either hydrogen peroxide, or peracetic acid, or mixtures thereof to improve thecolor of said member, the hydrogen-peroxide, or peracetic acid, or mixtures thereof being present in amount sufficient to enhance the bleaching.

2. The process of claim' 1 wherein said member is a fatty acid ester.

3.,The process of claim 1 wherein said member is an idized fatty acid ester.

4. The process of claim 3 wherein said epoxidized fatty acid ester is an epoxidized ester of an acid having eight to 22 carbon atoms.

5. The process of claim 4 wherein said irradiating is carried out in the presence of an alkaline material.

6. The process of claim 5 wherein the alkaline material is sodium hydroxide.

7. The process of claim 3 wherein said irradiating with ulepox traviolet light is carried out in the presence of an alkaline,

1 wherein said member is epoxis epox- 3.5 percent by weight based upon the member.

14. The process of claim 1 wherein said peroxy compound is present in an amount equal to about 0.5 percent by weight based upon the compound.

15. The process of claim 1 wherein said ultraviolet light has a wavelength between 2,500 and 3,500 angstroms.

16. The process of claim 1 wherein said irradiation is carried out at a temperature of about 38 C.

* l l I 5 

2. The process of claim 1 wherein said member is a fatty acid ester.
 3. The process of claim 1 wherein said member is an epoxidized fatty acid ester.
 4. The process of claim 3 wherein said epoxidized fatty acid ester is an epoxidized ester of an acid having eight to 22 carbon atoms.
 5. The process of claim 4 wherein said irradiating is carried out in the presence of an alkaline material.
 6. The process of claim 5 wherein the alkaline material is sodium hydroxide.
 7. The process of claim 3 wherein said irradiating with ultraviolet light is carried out in the presence of an alkaline material.
 8. The process of claim 7 wherein said alkaline material is sodium hydroxide.
 9. The process of claim 1 wherein said member is epoxidized tall oil ester.
 10. The process of claim 1 wherein said member is epoxidized soybean oil.
 11. The process of claim 1 which is carried out in the presence of hydrogen peroxide.
 12. The process of claim 1 which is carried out in the presence of peracetic acid.
 13. The process of claim 1 wherein said peroxy compound is present in an amount between about 0.1 percent and about 3.5 percent by weight based upon the member.
 14. The process of claim 1 wherein said peroxy compound is present in an amount equal to about 0.5 percent by weight based upon the compound.
 15. The process of claim 1 wherein said ultraviolet light has a wavelength between 2,500 and 3,500 angstroms.
 16. The process of claim 1 wherein said irradiation is carried out at a temperature of about 38* C. 